CN101743285B - UV curable ink with improved adhesion - Google Patents
UV curable ink with improved adhesion Download PDFInfo
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- CN101743285B CN101743285B CN200880021009.3A CN200880021009A CN101743285B CN 101743285 B CN101743285 B CN 101743285B CN 200880021009 A CN200880021009 A CN 200880021009A CN 101743285 B CN101743285 B CN 101743285B
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- ink
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- propenoate
- halogenated polyolefin
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Abstract
The present invention is drawn to photo-curable ink-jeet ink compositions, systems, and methods. One exemplary ink-jet ink composition includes a liquid vehicle, a milled pigment, a photo initiator and a halogenated polyolefin. In this embodiment, the addition of the halogenated polyolefin improves adhesion to a non-porous substrate or a low surface tension substrate such as polypropylene.
Description
Background technology
The printing ink that in inkjet industries, uses is liquid dispersion, solution or emulsion normally.The printing ink of known type comprises oil-based ink, non-aqueous solvent type printing ink, water color ink and solid ink.Ink jet printing process comprises the droplet of ink from the orifice plate of print head is ejected on the printed medium.Then,, for example, use heating or forced air with sedimentary droplets of ink or dry securely, perhaps dry under envrionment conditions.
Recently, through radiation curable ink, especially ultraviolet ray (UV) is solidified, and is more and more in vogue.In these cases, use special radiation-curable ink and image to solidify through being exposed to source of radiation.Term within the scope of the present invention " curing " refers to through being exposed to actinic radiation liquid such as printing ink changed into the solid process.The use of radiation-curable ink and solidification process becomes the alternative of mature common drying process apace.
With using the relevant problem of polytype printing ink is the weak binding property to the base material of non-porous or low surface tension such as Vestolen PP 7052, Vinylite, polyolefine etc.Vestolen PP 7052 for example is widely used in rigidity and semirigid purchase point is showed.Because polyacrylic surface is inert and has low surface tension, polar solvent such as Acrylic Acid Monomer can't be wetting it.The binding property that the result obtains is relatively poor.In addition, depend on the printing ink carrying capacity, when with ink printing on surface each other the time, the suitable cohesion between each ink lay on the base material then is lower than expected result.In addition, specifically for the UV curable ink, these printing ink usually use oligopolymer to prepare, and make the viscosity of printing ink be much higher than the viscosity of more typical solvent-borne type or water-based type printing ink.There is some difficulty in the injection of this type of viscous printing ink, and in addition, only under low frequency, sprays usually, therefore causes that print speed is slow.Because these printing ink are more tacky, so they are also usually at elevated temperatures, for example, be higher than about 40 ℃, sprayed.The temperature of this rising allow to otherwise have full-bodied printing ink some controls arranged, but can have influence on the print structure life-span of (comprising print head) unfriendly.Therefore, in UV curable ink field, also have bigger room for improvement, particularly work as it and relate to binding property non-porous to Vestolen PP 7052 or other, low surface tension substrate.
Detailed description of preferred embodiments
Before disclosing and describing particular embodiment of the present invention, it is understandable that the present invention is not limited to disclosed detailed process of this paper and material, these are change to a certain extent likewise.It is understandable that also the term that this paper uses only is used to describe the purpose of specific embodiments, and does not hope to have limited significance, because scope of the present invention is only limited accompanying claims and its equivalent.
To use following term when of the present invention describing and require.
Singulative " one ", " a kind of " and " being somebody's turn to do " comprise plural indicator, only if this paper clearly indication in addition.Therefore, for example, comprise mentioning of one or more these type of materials for mentioning of " pigment ".
Term " curing " refers to through being exposed to for example ultraviolet radiation of actinic radiation such as optical radiation liquid such as printing ink changed into the solid process.
Term " non-porous " or " low surface tension " can exchange use, and when mentioning base material such as media substrate, comprise the surface with more weak relatively water permeate, absorptivity and/or adsorptivity.Vinylite is considered to non-porous with other plastics sheet or film, metal, cated offset media, glass and other similar base material.According to these definition; Base material non-porous, low surface tension had improve the fusible light curable ink composite that is used for spray ink Printing and comprise the liquid low-melting ink vehicle, ground pigment, light trigger and the halogenated polyolefin that had for example ground in the triethylene glycol divinyl ether (DVE-3) in abrasive solvents be Chlorinated Polypropylene III for example.
In another embodiment; The ink-jet ink print system comprises base material non-porous or low surface tension such as Vestolen PP 7052; The jetted ink of light curable and light energy source can apply luminous energy to jetted ink in case this light energy source is configured to be printed on the non-porous base material.Luminous energy can comprise UV, IR and/or visible light.More particularly, luminous energy has the frequency and the energy level of the jetted ink that is suitable for solidifying light curable.Jetted ink comprises liquid low-melting ink vehicle, ground pigment, light trigger and halogenated polyolefin.
In another embodiment, the method for print image comprises that the jetted ink with light curable is ejected on the base material such as Vestolen PP 7052 or various other plastics and plastics verivate of non-porous or low surface tension.The jetted ink of light curable comprises liquid low-melting ink vehicle, ground pigment, light trigger and halogenated polyolefin.In case the jetted ink to light curable after another step is included in and is printed on the base material applies luminous energy, wherein luminous energy has the frequency and the energy level of the jetted ink that is suitable for solidifying this light curable.Can be used for more difficult for example non-porous base material of base material or the low surface tension substrate of printing though also it is pointed out that this system and method, these printing ink also are applicable to and are printed on the porous substrate.
According to general instruction of the present invention; When these printing ink normally during light curable; According to embodiments more of the present invention, this curing radiation can be that ultraviolet radiation and the printing ink that is used to print can be ultraviolet ray (UV) curable inks that contains UV activated initiator (also being known as the UV initiator).In these cases, curing radiation can be through the UV lamp, blue laser, ultraviolet laser, or the ultraviolet radiation that ultraviolet LED gave off.According to embodiments more of the present invention, curing radiation can be provided by the source according to the ultraviolet radiation of continuous-mode operation.According to other embodiments of the present invention, curing radiation can be provided by the source according to the flash of light or the ultraviolet radiation of burst mode operation.Other method that applies ultraviolet radiation also can adopt, and this is that those of skill in the art institute after considering disclosure thing is known.In other words, comprise that other cure system of those systems except that the UV cure system also can use, as long as employed radiation is suitable for causing the solidification process of jetted ink, for example, IR or visible light system.
Embodiments more of the present invention relate to or comprise the various compsns of ink-vapor recording fluidic of light curable.Therefore, this ink composite can comprise oligopolymer, polyfunctional acrylic ester and urea alkane propenoate.In addition, this ink composite is included in the existence of UV activated initiator can be carried out the propenoate of polyreaction down under the curable radiation of UV mixture.The non-limitative example of UV activated initiator comprises α keto-amine UV light trigger, like Ciba Irgacure 907, Ciba Irgacure 369 and Ciba Irgacure 379; Two acyl groups oxide compound (BAPO) UV light trigger of seeing, like Irgacure 907 or Irgacure 819, Darocur 4265 and Darocur TPO; α hydroxyketone UV light trigger such as Irgacure 184 and Darocur 1173; Comprising the light trigger that is with or without sensitizing agent, like Darocur ITX (2-isopropyl thioxanthone).As for propenoate, these compsns can be useful, because some propenoate have the height reactive behavior.In addition, some propenoate like mono acrylic ester, have good dissolving ability, high flexibility and lower glass transition temperatures (Tg).Low Tg can improve ink lay flexibility at room temperature.For example, in one embodiment, prepared identical printing ink is not compared when having mono acrylic ester, and the mono acrylic ester with the Tg that is lower than about 30 ℃ or 40 ℃ can be used in the flexibility of improving ink lay.
Mono acrylic ester has good binding property to plastics, and higher flexibility and thus is provided, even when plastics during by deflection, also can strengthen the binding property to plastics.Some mono acrylic esters can modification or some plastic basis material of swelling is non-porous with other, porous and/or low surface tension substrate such as SE (PVC), polymethylmethacrylate (PMMA) and polyolefine.This modification or the swelling of base material also can be improved binding property.Other propenoate such as triacrylate can help the printing ink low-shrinkage, good reactivity, and improved mechanical property and chemical-resistant, for example, molecular weight is high more, and cross-linking density is low more low more with shrinking percentage.Further, some propenoate such as diacrylate have high dissolving power and high reactivity, and this promotes the good adhesive property to non-porous surface.In other words, any suitable propenoate, or be used to realize the combination of the equilibrated propenoate of these or other performance, can both use.In addition, though scope of the present invention does not limit at this on the one hand, used propenoate also can be the propenoate of modification or derivatize.Example comprises the polyether glycol propenoate, polyoxyalkylene acrylate ester oligomer, cyclic trimethylolpropane methylal propenoate (CTFA), or amine propenoate.Especially, the amine propenoate like CN386 and Genomer5275, can be used in the cohesion of improvement between the jetted ink layer of printing, and after printing to the binding property of non-porous base material.
The relative quantity of the different components of ink-vapor recording compsn can change.For example, the relative quantity of light trigger can be about 0.1wt% to about 8wt% and in another embodiment, is that about 0.1wt% arrives about 4wt%.In other embodiments, the relative quantity of light trigger is about 0.2wt% to about 2wt%, or even about 0.2wt% arrive about 1wt%.In other embodiments, the relative quantity of halogenated polyolefin is about 0.5wt% to about 4wt%, or even about 1wt% arrive about 2.5wt%.The relative quantity of various other components that likewise, can exist can be 1wt%-30wt%.For example, propenoate exists to the amount of 8wt% with 1wt%.Perhaps or in addition, 5wt% to the vinyl of the relative quantity of 25wt% in oneself amide can be used to improve the binding property of ink lay equally to base material.
Compsn can further comprise any tinting material, for example pigment such as ground pigment and the additive of choosing wantonly such as dispersion agent, wetting agent, tensio-active agent, flow agent etc.The non-limitative example that can be used in the pigment in the example embodiment prescription of the present invention comprises E4GN Yellow 150, RT-355-Magenta, Hostaperm Blue P-BFS Cyan; Sunfast Black 7, solid blue (fast blue) BG of PV, PV fast red (fast red) E5B; PV fast yellow (fast yellow) HG; Permanent black R30, other pigment, or the mixture of multiple pigment.Generally speaking, be used for the present invention's the not special restriction of black and coloured pigment, and mineral dye or pigment dyestuff can use.Suitable mineral dye comprises for example titanium oxide, cobalt blue (CoO-Al
2O
3), chrome yellow (PbCrO
4) and red stone.Suitable pigment dyestuff comprises that for example azo pigment encircles pigment (for example, phthalocyanine pigments perylene dye, perynone pigment, anthraquinone pigment, quinacridone pigment triazine dioxin pigment, thioindigo pigment, iso-dihydro-indole pigment and quinophthalones pigment) more, and the dyestuff inner complex (for example; Basic dye type chelates and acidic dye type chelate), nitropigments, nitroso pigments, or the like.Combine with these or other pigment, the non-limitative example that can be used in the dispersion agent in the illustrative embodiments of the invention prescription comprises Solsperse 32000, and Solsperse 39000; Solsperse 5000, and Solsperse 22000, and Disperbryk 163; Disperbyk 167, and Disperbyk 168, and Disperbyk 180; Disperbyk 190, and Disperbyk 191, or the like.
As what mentioned, inkjet ink composition randomly also comprises wetting agent.The non-limitative example of this type of wetting agent comprises silicone polyether propenoate such as Tego Rad 2200N, Tego Rad 2300 and Byk358N.This printing ink also can comprise polyether-modified YSR 3286 wetting agent, like Byk333, and Byk307 and Silwet L-7604.If use, wetting agent can be with the 0.01%-of inkjet ink composition the amount of about 10% (weight) exist.
The specific characteristic of light curable printing ink of the present invention is to the media substrate of non-porous and low surface tension such as the improvement binding property of plastics.These printing ink are constructed in one way, and this mode allows by means of halogenated polyolefin such as Chlorinated Polypropylene III, and base material non-porous after ink-jet is to base material, low surface tension is bonded in printing ink better.As what mentioned, inkjet ink composition can be ejected on the media substrate.In addition, system and method for the present invention comprises media substrate.The media substrate that is used for the present invention comprises non-porous and media substrate low surface tension.Non-limitative example comprises plastics, PVC, flag (banner) paper and Vestolen PP 7052, and synthetic paper, like the Yupo synthetic paper.Flag paper is through specifically being configured to print flag, having smooth surface, and is designed to color printing usually.The Yupo synthetic paper is an example of synthetic paper.Yupo is Vestolen PP 7052 water-repellancy, anti-contamination and that very high strength is arranged and particular type weather resistance.
Light curable printing ink of the present invention is not limited to one type polyolefine.The non-limitative example of halogenated polyolefin can comprise chlorinatedpolyethylene, Chlorinated Polypropylene III, chlorinated polybutylenes, bromination Vilaterm, bromination Vestolen PP 7052, bromination polybutylenes, fluorinated polyethylene, fluorinated polypropylene and fluoridize polybutylenes.Therefore, pointed as these embodiment, though chlorine is the preferred halogen that is used for the present invention, other halogen that has with the similar chemical property of teachings of the present invention can both use.Non-limitative example is bromine or fluorine.
Another specific characteristic of light curable printing ink of the present invention is that they can be after preparation; Need before using and/or in the process, from printing ink, not remove air or other gas, even under high injection frequency, for example greater than 18-20KHz; Greater than 25KHz, or even greater than 29KHz.Should be noted that the fact that these printing ink can spray is not restricted to high injection frequency system with these printing ink under high frequency.These printing ink also can spray under low relatively injection frequency equally.In other words, general, for UV and other light curable printing ink, this type of printing ink embodies usually and is characterised in that the high gas content that disturbs ink jet process.Printing ink of the present invention is characterised in that to have unusual low gas content.In some embodiments, the process of in the grinding of pigment, using has been contributed this advantage.For example, through with specific solvent ground pigment, can minimize or eliminate generation of air or gas or release.The example of the suitable solvent that is used to realize this goal is triethylene glycol divinyl ether (DVE-3), and it is an example of abrasive solvents, and this solvent allows printhead under high injection frequency, to work, and need not the printing ink degassing formerly.It should be noted that DVE-3 only is an example of this kind solvent, and depend on this pigment, other solvent also can provide similar function.Therefore, other solvent that is used to grind that also with good grounds embodiment of the present invention can be used is selected.In one aspect of the invention, it is non-reacted relatively each other that pigment and abrasive solvents can be chosen to them, or solvent can be chosen to minimum gas dissolving ability is arranged to there not being the gas dissolving ability for granules of pigments.Also it should be noted that; The dissolved oxygen value that the UV printing ink of prior art has in printing ink usually is 6-8ppm (weight); And printing ink of the present invention-its use pigment is had a low gas dissolving ability abrasive solvents for example DVE-3-can have the 5ppm of being lower than (weight); The dissolved oxygen value of 3-5ppm (weight) for example, this can reduce the reactivity of printing ink.
Usually, in order to produce full-colour image, printing ink external member (ink set) can comprise cyan, magenta and yellow inkjet ink composition, or comprises cyan, light cyan, magenta, shallow magenta and yellow inkjet ink composition in addition.Black ink also can be included in these printing ink external members.Other combination also is possible.
Embodiment
In the following example of ink composite, component identification is a percentage ratio by weight, according to specified.It is to be noted the scope that the following example does not limit the present invention in any way.In other words, the following example is used to illustrate abundant known embodiment of the present invention at present.Yet, it will be appreciated that the following example is the only example of the application of the principles of the present invention or illustrates.Under the prerequisite that does not deviate from the spirit and scope of the present invention, those technician in this area can design a lot of improvement and alternative compsn, method and system.Accompanying claims is used to cover this type of improvement and arrangement.Therefore, although abovely specifically described the present invention, the following example provides and has been considered to most realistic and the relevant further details of those contents embodiment preferred of the present invention at present.
Embodiment 1
| Composition | Wt％ |
| Ethoxylation (15) Viscoat 295 | 20％ |
| Diacrylate 1,6-pinakon ester | 27.7％ |
| The vinylformic acid tetrahydro furfuryl ester | 25％ |
| The amine propenoate | 2％ |
| Chlorinated Polypropylene III | 2％ |
| The 1-butanone, 2-(dimethylamino)-2-[(4-aminomethyl phenyl) methyl]-1-[4-(4-morpholinyl) phenyl | 2％ |
| 2,4,6-trimethylbenzoyl phenylphosphine oxide | 2％ |
| The isomer mixture of 2-isopropyl thioxanthone and 4-isopropyl thioxanthone | 2％ |
| Copper, [29H, 31H-phthalocyanine close (2)-κ N29, κ N30, κ N31, κ N32]-, (SP-4-1)-(9CI) | 2％ |
| Divinyl ether | 7％ |
| Polymeric dispersant | 1％ |
| The silicone polyether propenoate | ?0.2％ |
Embodiment 2
| Composition | Wt％ |
| Ethoxylation (15) Viscoat 295 | 20％ |
| Diacrylate 1,6-pinakon ester | 27.7％ |
| The vinylformic acid tetrahydro furfuryl ester | 25％ |
| The amine propenoate | 2％ |
| Chlorinated Polypropylene III | 2％ |
| The 1-butanone, 2-(dimethylamino)-2-[(4-aminomethyl phenyl) methyl]-1-[4-(4-morpholinyl) phenyl | 2％ |
| 2,4,6-trimethylbenzoyl phenylphosphine oxide | 2％ |
| The isomer mixture of 2-isopropyl thioxanthone and 4-isopropyl thioxanthone | 2％ |
| Copper, [29H, 31H-phthalocyanine close (2-)-κ N29, κ N30, κ N31, κ N32]-, (SP-4-1)-(9CI) | 2％ |
| Divinyl ether | 7％ |
| Polymeric dispersant | 1％ |
| The silicone polyether propenoate | 0.2％ |
Embodiment 3
| Composition | Wt％ |
| Ethoxylation (15) Viscoat 295 | 20％ |
| Diacrylate 1,6-pinakon ester | 27.7％ |
| The vinylformic acid tetrahydro furfuryl ester | 20％ |
| Caprolactam | 5％ |
| The amine propenoate | 2％ |
| Chlorinated Polypropylene III | 2％ |
| The 1-butanone, 2-(dimethylamino)-2-[(4-aminomethyl phenyl) methyl]-1-[4-(4-morpholinyl) phenyl | 2％ |
| 2,4,6-trimethylbenzoyl phenylphosphine oxide | 2％ |
| The isomer mixture of 2-isopropyl thioxanthone and 4-isopropyl thioxanthone | 2％ |
| Copper, [29H, 31H-phthalocyanine close (2-)-κ N29, κ N30, κ N31, κ N32]-, (SP-4-1)-(9CI) | 2％ |
| Divinyl ether | ?7％ |
| Polymeric dispersant | ?1％ |
| The silicone polyether propenoate | ?0.2％ |
Embodiment 4
| Composition | Wt％ |
| Six functionalized urea alkane propenoate | 20％ |
| Diacrylate 1,6-pinakon ester | 27.7％ |
| The vinylformic acid tetrahydro furfuryl ester | 25％ |
| The amine propenoate | 2％ |
| Chlorinated Polypropylene III | 2％ |
| The 1-butanone, 2-(dimethylamino)-2-[(4-aminomethyl phenyl) methyl]-1-[4-(4-morpholinyl) phenyl | 2％ |
| 2,4,6-trimethylbenzoyl phenylphosphine oxide | 2％ |
| The isomer mixture of 2-isopropyl thioxanthone and 4-isopropyl thioxanthone | 2％ |
| Copper, [29H, 31H-phthalocyanine close (2-)-κ N29, κ N30, κ N31, κ N32]-, (SP-4-1)-(9CI) | 2％ |
| Divinyl ether | 7％ |
| Polymeric dispersant | 1％ |
| The silicone polyether propenoate | 0.2％ |
According to exemplary embodiment of the present invention, ink formulations is applied on the polypropylene base and at about 200mj/cm
2Following UV solidifies.The thickness of ink lay is about 12.5 microns.The viscosity of printing ink is lower than 30cp, and surface tension is that 26.9 dyne/cm and granularity are lower than 1 micron.The cured layer of printing ink does not show that ink lay peels off or ftracture and born standard abrasion and adhesive tape test.
Although illustrated and described some characteristic of the present invention here, many improvement substitute, and variation and equivalent feature are conspicuous for those skilled in the art.Therefore it is understandable that accompanying claims is used to cover whole these type of improvement and the variation within the true spirit of the present invention.
Claims (12)
1. base material non-porous, low surface tension had the improved fusible light curable ink composite that is used for spray ink Printing; Said composition comprises: the liquid low-melting ink vehicle; Ground pigment; Light trigger and halogenated polyolefin, wherein ground pigment is in comprising the abrasive solvents of triethylene glycol divinyl ether, to grind.
2. the compsn of claim 1, wherein said composition comprises the have second-order transition temperature mono acrylic ester of (Tg), its identical printing ink prepared with there not being mono acrylic ester is compared, and has improved the flexibility of ink lay.
3. the compsn of claim 1, wherein said composition comprises the amine propenoate.
4. the compsn of claim 1, wherein this halogenated polyolefin is a chlorinatedpolyolefins.
5. the compsn of claim 1, wherein this halogenated polyolefin comprises Chlorinated Polypropylene III.
6. jetted ink print system, it comprises:
A) media substrate non-porous, low surface tension;
B) jetted ink of at least a light curable, this printing ink comprises:
I) liquid low-melting ink vehicle,
Ii) ground pigment,
Iii) light trigger and
Iv) halogenated polyolefin, wherein ground pigment is in comprising the abrasive solvents of triethylene glycol divinyl ether, to grind; With
C) in case be configured to be printed on the light energy source that can apply luminous energy on the base material to jetted ink, said luminous energy has frequency and the energy level that is suitable for solidifying this light curable jetted ink.
7. the system of claim 6, wherein this system comprises the jetted ink of two kinds of light curables, has the tone or the colour density that differ from one another separately.
8. the system of claim 6, wherein the jetted ink of at least a light curable comprises the amine propenoate, and its content can improve the cohesion between the light curable jetted ink layer of printing.
9. the system of claim 6, wherein the jetted ink of at least a light curable comprises at least a in caprolactam and the propenoate.
10. the system of claim 6, wherein halogenated polyolefin is selected from halogenated polyethylene, halogenation Vestolen PP 7052 and halogenation polybutylenes.
11. the system of claim 6, wherein halogenated polyolefin comprises Chlorinated Polypropylene III.
12. the system of claim 6, wherein media substrate is a plastic basis material.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/821,258 US8857961B2 (en) | 2007-06-21 | 2007-06-21 | UV curable ink with improved adhesion |
| US11/821,258 | 2007-06-21 | ||
| PCT/US2008/067927 WO2008157836A2 (en) | 2007-06-21 | 2008-06-23 | Uv curable ink with improved adhesion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101743285A CN101743285A (en) | 2010-06-16 |
| CN101743285B true CN101743285B (en) | 2012-09-26 |
Family
ID=40136014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880021009.3A Expired - Fee Related CN101743285B (en) | 2007-06-21 | 2008-06-23 | UV curable ink with improved adhesion |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8857961B2 (en) |
| EP (1) | EP2167592B1 (en) |
| JP (1) | JP2010530922A (en) |
| CN (1) | CN101743285B (en) |
| TW (1) | TWI468473B (en) |
| WO (1) | WO2008157836A2 (en) |
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| US5919834A (en) * | 1995-08-11 | 1999-07-06 | Illinois Tool Works Inc. | U-V cured heat activated labels for substrates and preparation methods therefore |
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| EP2167592B1 (en) | 2014-05-07 |
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| JP2010530922A (en) | 2010-09-16 |
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